Bear in mind that Mr. Larsen sold e-Loan for approx $300 million.
But the $300M from Popular didn't go to Larsen. E-loan was already a public company at that time. I looked up some of the history tonite.
1997 Chris Larsen & Janina Pawlowski found E-loan.
1998 E-loan gets venture capital.
1999 Went public. That's quick! This was the peak of the internet bubble!
2005 Popular (parent of Banco Popular) bought the already-public company E-loan for $300M in cash.
2007 E-loan laid-off 500 employees.
2008, Popular announced that E-loan would no longer originate mortgages (its original purpose), but would continue to sell CDs.
After the venture capital, Larsen surely owned a minority position. Maybe 10% to 30%? I don't know how much the VCs took or how much was distributed to employees. After the IPO he owned an even smaller fraction. I have no idea when he sold his stock, or whether he held it until the buyout. At one point soon after the IPO E-loan stock was worth over $1B, but then dropped big. The documents re the IPO and Larsen's stock sales are public info, so one could research them thru SEC, but it would take a lot of digging.
Then he had to pay taxes.
The range of possibilities here is large. Most internet entrepreneurs did NOT sell at the peak of their company stock price. My guess: Maybe he got out with $20M to $100M or so, eh?
Still your point is valid.
PS: cute old article about the E-loan IPO:
http://www.businessweek.com/1999/99_36/b3645001.htm